Liston et al., U.S. Pat. Nos. 4,632,771 and 4,643,838 for NORMALLY LIQUID C.sub.18 TO C.sub.24 MONOALKYL CATECHOLS refer to normally liquid lubricating oil additives which provide both antioxidant and friction-modifying properties when added to lubricating oil. In particular, these patents relate to C.sub.18 to C.sub.24 alkyl catechol lubricating oil additives which are normally liquid at typical storage temperatures.
Werner et al., U.S. Pat. No. 4,265,833 for a PROCESS FOR THE PREPARATION OF HYDROXY-DIPHENYLAMINES refers to a process for the preparation of hydroxy-diphenylamines by condensation of dihydroxybenzene with an excess amount of primary aromatic amine in the presence of a catalytic amount of an acid at elevated temperature, wherein the excess aromatic amine and the reaction product is distilled off from the reaction mixture in the presence of a base.
Coupland et al., U.S. Pat. No. 3,592,820 for SUBSTITUTED CATECHOL SALTS OF BENZOTRIAZOLES OR PHENYLHYDRAZINES refers to a compound which may be produced by reaction of substituted catechol with phenylhydrazine, substituted phenylhydrazine, benzotriazole, or substituted benzotriazole. The reaction may be carried out in an inert solvent, such as a hydrocarbon. The compounds are useful as antioxidants in lubricant compositions.
Small, Jr. et al., U.S. Pat. No. 5,061,390 for DIETHYLAMINE COMPLEXES OF BORATED ALKYL CATECHOLS AND LUBRICATING OIL COMPOSITIONS CONTAINING THE SAME refers to lubricating oils containing a borated alkyl catecholdiethylamine complex effective in reducing oxidation, wear, and deposits in internal combustion engines.
Davis, U.S. Pat. No. 4,663,063 for ALKYL PHENOL AND AMINO COMPOUND COMPOSITIONS AND TWO-CYCLE ENGINE OILS AND FUELS CONTAINING SAME refers to a composition comprising the combination of (A) at least one alkyl phenol of the formula EQU (R).sub.a --Ar--(OH).sub.b
wherein each R is independently a substantially saturated hydrocarbon-based group of an average of at least about 10 aliphatic carbon atoms; a and b are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b, and c does not exceed the unsatisfied valences of Ar; and Ar is an aromatic moiety which is a single ring, a fused ring or a linked polynuclear ring having 0 to 3 optional substituents selected from the group consisting essentially of lower alkyl, lower alkoxyl, carboalkoxy methylol or lower hydrocarbon-based substituted methylol, nitro, nitroso, halo and combinations of said optional substituents, and (B) at least one amino compound with the proviso that the amino compound is not an amino phenol. Lubricants and lubricating oil-fuel mixtures for two-cycle engines which include the above compositions, and methods for lubricating two-cycle engines are also disclosed.
When a polymer chain is functionalized with a hydroxyaromatic, it is well known in the art to derivatize the alkylated hydroxyaromatic with an amine in the presence of an aldehyde. This derivatization is known as a Mannich Base reaction. In the present invention, dihydroxyaromatics may be derivatized with amines without the use of an aldehyde--thereby saving the expense of utilizing a reagent that is consumed in the reaction.